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Sean Diddy Combs sex trafficking trial live: Bombshell allegations from day two

Cassie Ventura has detailed her “humiliating” alleged encounters with Sean “Diddy” Combs. Here are the bombshells from day two of the trial. Warning: Graphic

What you need to know about the Sean Combs trial

Singer Cassie Ventura was the prosecution’s star witness in the blockbuster sex trafficking trial of music mogul Sean “Diddy” Combs.

In an emotional morning of testimony, the heavily pregnant 38-year-old said she was a naive and sexually inexperienced 19-year-old when she met Combs who was 17 years her senior.

Ms Ventura said she quickly became enamoured with the charismatic rapper but their fun and happy relationship became dark when he began physically abusing her and introduced her to “freak off” sex parties where he would watch as she had sex with male escorts.

Here are the bombshells from day two.

DAY 2:

‘COMBS WOULD URINATE ON VENTURA’

Combs would allegedly urinate on Ventura, sometimes at the same time he directed a male prostitute to urinate on her during their “freak-offs,’’ she testified.

Sometimes Sean, he himself or the escort, would urinate on me,’’ she said. “Sean urinated at the same time.”

Cassie Ventura walks out of the courtroom past Sean Diddy Combs after testifying. PictureL Elizabeth Williams via AP
Cassie Ventura walks out of the courtroom past Sean Diddy Combs after testifying. PictureL Elizabeth Williams via AP

She said that once when an escort peed into her mouth during the “humiliating’’ encounters, “It was overwhelming. I choked,’’ the witness said. “Too much urine in my mouth. … Laid on a position on the floor [in a position] that I couldn’t easily get out of.”

Ventura said she put up her hands to get Diddy to stop the escort but nothing was done.

‘SEAN INTRODUCED ME TO VOYEURISM’

“Within the first year of our relationship Sean introduced to me this sexual encounter he called voyeurism where he would watch me have sexual intercourse with a third party, specifically another man,” she said.

“It basically entails the hire of an escort and setting up this experience so I could perform for Sean.”

Ms Ventura stopped to compose herself while describing the first time Combs proposed the act, saying her stomach dropped.

“I didn’t have a concept of how that would be a turn on … I was confused, nervous, but loved him very much and wanted to make him happy”.

She said she quickly decided it was something she didn’t want to do.

“Again I was just in love and wanted to make him happy,” Ms Ventura said when asked why she kept participating.

“I didn’t feel like I had much of a choice, I didn’t know what ‘no’ could be or what ‘no’ could turn into.”

Sean
Sean "Diddy" Combs with Cassandra "Cassie" Ventura at the Met Gala in 2017. Picture: Getty Images

‘COMPLETELY INEXPERIENCED’: 21-Y.O. VENTURA FLED DIDDY’S ADVANCES

The pair dated on and off for more than a decade after meeting when Combs signed Ventura, a model and singer, to his label Bad Boy Records for a 10 album deal.

Ms Ventura is the star witness in the federal racketeering and sex trafficking case against Combs who has pleaded not guilty to the charges against him.

The court heard the pair were first romantically involved when Combs kissed Ms Ventura in the bathroom of his Las Vegas hotel room on her 21st birthday after the MTV Music Awards.

Ms Ventura said she was young, naive and confused by the sexual advance from the powerful music boss and she ran from the hotel room crying.

ORAL SEX IN THE TRUMP HOTEL

In the months after that, she said Combs would invite her to his hotel room at the Trump hotel in New York City where he lived while his apartment was being renovated and it was there he introduced her to oral sex.

“I was just so young I didn’t even have the vocabulary for the things we talked about … (I was) just completely sexually inexperienced at the time,” she said.

Ms Ventura said she was excited about the prospect of spending time with the business mogul.

“I wanted to be around Sean for the same reasons as everyone else at the time, he was this exciting, entertaining, fun guy who also happened to have my career in his hands,” she said.

“It felt special because not a lot of people got to spend that kind of time around him.”

Model Cassie Ventura and rapper boyfriend P Diddy in an undated photo. Picture: Instagram
Model Cassie Ventura and rapper boyfriend P Diddy in an undated photo. Picture: Instagram

DIDDY GAVE VENTURA ECSTASY ON A BOAT

She said the pair first had sex when Combs hired a boat in Miami. He introduced her to drugs on that trip, giving her an ecstasy pill that she said made her feel euphoric.

Prior to that, she had smoked marijuana and drank wine, and had accidentally had ecstasy when she unknowingly drank another person’s Gatorade laced with drugs.

After the Miami trip, they started a relationship that she believed was monogamous but later learned was not.

“After Miami I really fell in love with him,” Ms Ventura said.

“We had fun, it was kind of like my first real adult relationship.”

The Manhattan federal court was shown a series of photos of the pair in the 2000s, on red carpets, in his car, at a strip club and other events.

Ms Ventura said over time, she began to experience a different side to him that was abusive and controlling but told the jury “there was still love there”.

Combs would control everything about her life, including what she wore, who she went, who she talked to and her career.

Ms Ventura said if she didn’t answer a call or text message, Combs would repeatedly call and message until she answered, or send his bodyguards and assistants to physically find her.

‘HIT HER IN THE FACE’

The violence also escalated and she said during the relationship she was hit, kicked, thrown to the ground and stomped on by Combs.

“You make the wrong face and the next thing I know I was getting hit in the face,” she said.

“If I wasn’t smiling at him the way he wanted, if I just looked a certain way…”.

She said the relationship was marked by jealousy on both sides and they were both unfaithful during the decade-long on and off romance.

“I was insanely jealous but also super young and I didn’t get it at all, I was young and jealous,” she said.

“I didn’t get that was him – as he would say, ‘I’m Puff Daddy and Puff Daddy has many women’.”

CASSIE TASKED WITH FINDING ‘BLACK MALE WITH LARGE PENIS’

Ms Ventura testified that Combs tasked her with finding the male escorts for “freak-offs”, which she initially sourced through classified companies Craigslist and Backpage.

She said she answered ads on Craigslist for male sex workers who Combs preferred to be “a black male with a large penis.”

RECOVERING FROM ‘FREAK-OFFS’ TOOK DAYS

Ms Ventura, who goes by the recording name Cassie, said despite her 10 album deal with Bad Boy Records, recording hundreds of songs and her relationship with the head of the company, Combs only allowed her to release one of the albums promised.

She said when she wasn’t recording music, she was recovering from days long “freak offs”.

“Plainly the freak-offs became a job where there was no space to do anything but recover and try to feel normal again,” Ms Ventura said.

She said the sex parties ranged anywhere from 36 to 72 hours, with the longest one lasting for four days.

Ms Ventura said recovering from sex with strangers, dehydration and the drugs took days.

Sean ‘Diddy’ Combs is on trial for charges of sex trafficking and racketeering. Picture: AFP
Sean ‘Diddy’ Combs is on trial for charges of sex trafficking and racketeering. Picture: AFP

DAY 1:

The mammoth trial against rapper and record producer Sean Combs, known as Diddy, P. Diddy and Puff Daddy, began in New York on Tuesday.

Hundreds of people packed into the Manhattan courthouse to witness the 55-year-old’s trial on charges of sex trafficking and racketeering.

Here are the bombshell moments from day one of the trial.

‘I SAW HIM HIT HER’: MALE ESCORT TESTIFIES

One of the men allegedly paid to have sex with Combs’ then-girlfriend Cassie Ventura was 41-year-old Daniel Philip.

Mr Philip testified that he was asked to perform as a stripper at a bachelorette party at the Gramercy Park Hotel in Manhattan but when he arrived, Ms Ventura handed him thousands of dollars and asked if he could rub baby oil on her and give her a massage.

The escort said he and Ms Ventura had sex while Combs sat in a corner and masturbated.

Daniel Philip testifies on the witness stand on the first day of Sean Diddy Combs' trial in Manhattan federal court, Monday, May 12, 2025, in New York. Picture: Elizabeth Williams via AP
Daniel Philip testifies on the witness stand on the first day of Sean Diddy Combs' trial in Manhattan federal court, Monday, May 12, 2025, in New York. Picture: Elizabeth Williams via AP

Mr Philip said he met with the couple multiple times after that at various hotels in New York, and at both their homes where he would have sex with Ms Ventura while Combs watched and directed them.

“He was always sitting in a corner masturbating,” Mr Philip said of Combs’ involvement.

The escort said on one occasion, Ms Ventura asked him to urinate on her while Combs watched but said he did it wrong.

“Cassie (Ms Ventura) was actually the one that asked me urinate on her,” Mr Philip said. “She asked me if I had ever done that before. She told me to do it.”

Mr Philip said his association with the couple ended because he could no longer become aroused “after the first time I saw him hit her”.

Cassie Ventura and Sean Combs pictured in May 2015 in New York City. Picture: Larry Busacca/Getty Images
Cassie Ventura and Sean Combs pictured in May 2015 in New York City. Picture: Larry Busacca/Getty Images

He said Combs grabbed Ms Ventura by her hair and dragged her to the bedroom.

“She was screaming,” Mr Philip said. “I could hear what sounded like him slapping her … and him (saying) ‘bitch, when I tell you to come here you come now, not later’.”

‘DEVILISH STARE’: HOTEL SECURITY GUARD ON COMBS

Israel Florez, a security guard at the InterContinental Hotel in Los Angeles and now a police officer, testified that he was in the InterContinental Hotel in Century City during the 2016 assault of Ms Ventura.

“I received a call … saying there’s a woman in distress on the sixth floor,” he said.

When asked by prosecutors who he saw on the floor, he said he observed a man and woman in the elevator lobby.

“Mr Combs – Sean Combs,” he said, before identifying Combs in the courtroom.

First witness Intercontinental Security Officer Israel Florez testifies on the witness stand. Picture: Elizabeth Williams via AP
First witness Intercontinental Security Officer Israel Florez testifies on the witness stand. Picture: Elizabeth Williams via AP

Combs had a “devilish” look on his face following his alleged brutal caught-on-video beating of Ventura, jurors heard.

“He was on the chair, slouched down and he [had] a blank stare. As soon as I walked out, the best way I can describe it is a devilish stare. He was just looking at me … Looking at me with no movement,” Florez testified.

Cassie looked “scared,” Florez told the jury. “She had her hoodie on. She was pretty much covered up. I couldn’t see her face.”

Combs offered Florez a “stack of money” topped with a $100-bill, telling him to “take care of this.”

Originally published as Sean Diddy Combs sex trafficking trial live: Bombshell allegations from day two

Original URL: https://www.themercury.com.au/news/world/north-america/sean-diddy-combs-sex-trafficking-trial-live-male-escorts-shock-testimony/news-story/ed7492b0f3abc856f95194690c4e9d5b